5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans via prins-type cyclization

Authors
Chavre, Satish N.Choo, HyunahCha, Joo HwanPae, Ae NimChoi, Kyung IlCho, Yong Seo
Issue Date
2006-08-03
Publisher
AMER CHEMICAL SOC
Citation
ORGANIC LETTERS, v.8, no.16, pp.3617 - 3619
Abstract
5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans, were synthesized from homopropargylic alcohols with terminally substituted alkynes and various aldehydes via Prins-type cyclization. It is of interest that the exocyclic vinyl cation generated as a result of Prins-type cyclization could be trapped as a vinyl triflate when CH2Cl2 was used as a solvent, whereas in ethereal solution the vinyl cation underwent hydrolysis to give the corresponding ketone product.
Keywords
STEREOCONTROLLED PREPARATION; ACID; TETRAHYDROPYRAN; EPIMERIZATION; SUPPRESSION; STEREOCONTROLLED PREPARATION; ACID; TETRAHYDROPYRAN; EPIMERIZATION; SUPPRESSION; tetrahydrofuran; 5-exocyclic; prins type cyclization
ISSN
1523-7060
URI
https://pubs.kist.re.kr/handle/201004/135247
DOI
10.1021/ol061528x
Appears in Collections:
KIST Article > 2006
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